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Access to Chiral Hydropyrimidines through Palladium‐Catalyzed Asymmetric Allylic C−H Amination
Author(s) -
Wang PuSheng,
Shen MengLan,
Wang TianCi,
Lin HuaChen,
Gong LiuZhu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709681
Subject(s) - allylic rearrangement , amination , chemistry , phosphoramidite , intramolecular force , palladium , stereoselectivity , enantioselective synthesis , catalysis , sulfonyl , combinatorial chemistry , ligand (biochemistry) , medicinal chemistry , stereochemistry , organic chemistry , receptor , dna , biochemistry , alkyl , oligonucleotide
A palladium‐catalyzed asymmetric intramolecular allylic C−H amination controlled by a chiral phosphoramidite ligand was established for the preparation of various substituted chiral hydropyrimidinones, the precursors of hydropyrimidines, in high yields with high enantioselectivities. In particular, dienyl sodium N ‐sulfonyl amides bearing an arylethene‐1‐sulfonyl group underwent a sequential allylic C−H amination and intramolecular Diels–Alder (IMDA) reaction to produce chiral fused tricyclic tetrahydropyrimidinone frameworks in high yields and with high levels of stereoselectivity. Significantly, this method was used as the key step in an asymmetric synthesis of letermovir.